AU2007227203B2 - 6,7,8, 9 -tetrahydro- 5H- pyrimido [4, 5-d] azepin-4-yl] -amine derivatives as modulators of TRPVL for the treatment of pain - Google Patents

6,7,8, 9 -tetrahydro- 5H- pyrimido [4, 5-d] azepin-4-yl] -amine derivatives as modulators of TRPVL for the treatment of pain Download PDF

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Publication number: AU2007227203B2
Authority: AU; Australia
Prior art keywords: trifluoromethyl; tetrahydro; phenyl; pyridin; pyrimido
Prior art date: 2006-03-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Ceased

Application number

AU2007227203A

Other languages

English (en)

Other versions

AU2007227203A1 (en

Inventor

Brett D. Allison

Bryan James Branstetter

James Guy Breitenbucher

Michael D. Hack

Natalie A. Hawryluk

Alec D. Lebsack

Kelly J. Mcclure

Jeffrey E. Merit

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Janssen Pharmaceutica NV

Original Assignee

Janssen Pharmaceutica NV

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-03-21

Filing date

2007-03-21

Publication date

2013-01-10

2007-03-21 Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV

2007-09-27 Publication of AU2007227203A1 publication Critical patent/AU2007227203A1/en

2013-01-10 Application granted granted Critical

2013-01-10 Publication of AU2007227203B2 publication Critical patent/AU2007227203B2/en

Status Ceased legal-status Critical Current

2027-03-21 Anticipated expiration legal-status Critical

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208000002193 Pain Diseases 0.000 title claims abstract description 29
238000011282 treatment Methods 0.000 title claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 237
238000000034 method Methods 0.000 claims abstract description 84
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
208000035475 disorder Diseases 0.000 claims abstract description 35
102000003566 TRPV1 Human genes 0.000 claims abstract description 33
101150016206 Trpv1 gene Proteins 0.000 claims abstract description 33
201000010099 disease Diseases 0.000 claims abstract description 23
230000001404 mediated effect Effects 0.000 claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
206010011224 Cough Diseases 0.000 claims abstract description 8
208000003251 Pruritus Diseases 0.000 claims abstract description 7
208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 6
208000006673 asthma Diseases 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 424
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 411
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 278
125000000217 alkyl group Chemical group 0.000 claims description 202
-1 -CO 2 H Chemical group 0.000 claims description 196
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 129
125000001424 substituent group Chemical group 0.000 claims description 121
150000001412 amines Chemical group 0.000 claims description 87
150000003839 salts Chemical class 0.000 claims description 85
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 78
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
229910052757 nitrogen Inorganic materials 0.000 claims description 59
PAXQXJDYVORMOO-UHFFFAOYSA-N 2-methyl-4-(trifluoromethyl)aniline Chemical group CC1=CC(C(F)(F)F)=CC=C1N PAXQXJDYVORMOO-UHFFFAOYSA-N 0.000 claims description 48
229940002612 prodrug Drugs 0.000 claims description 45
239000000651 prodrug Substances 0.000 claims description 45
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 41
RNYCYVMKIPDJGB-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepin-4-amine Chemical compound C1CNCCC2=C1N=CN=C2N RNYCYVMKIPDJGB-UHFFFAOYSA-N 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 36
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
239000003795 chemical substances by application Substances 0.000 claims description 35
125000004093 cyano group Chemical group *C#N 0.000 claims description 34
125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 34
125000004076 pyridyl group Chemical group 0.000 claims description 33
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 29
125000000714 pyrimidinyl group Chemical group 0.000 claims description 28
125000003396 thiol group Chemical group [H]S* 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
150000001408 amides Chemical class 0.000 claims description 20
230000000694 effects Effects 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 17
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 17
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
125000003386 piperidinyl group Chemical group 0.000 claims description 17
125000003373 pyrazinyl group Chemical group 0.000 claims description 17
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 17
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 15
125000002757 morpholinyl group Chemical group 0.000 claims description 15
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
125000001309 chloro group Chemical group Cl* 0.000 claims description 14
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
239000005711 Benzoic acid Substances 0.000 claims description 13
229940047889 isobutyramide Drugs 0.000 claims description 13
125000002950 monocyclic group Chemical group 0.000 claims description 13
229910052705 radium Inorganic materials 0.000 claims description 13
229910052701 rubidium Inorganic materials 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
125000004193 piperazinyl group Chemical group 0.000 claims description 11
125000002098 pyridazinyl group Chemical group 0.000 claims description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
229910003827 NRaRb Inorganic materials 0.000 claims description 10
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
150000004985 diamines Chemical class 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
125000000539 amino acid group Chemical group 0.000 claims description 9
125000004069 aziridinyl group Chemical group 0.000 claims description 9
125000001246 bromo group Chemical group Br* 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 9
ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 8
125000005907 alkyl ester group Chemical group 0.000 claims description 8
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
238000001212 derivatisation Methods 0.000 claims description 8
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 8
150000004702 methyl esters Chemical class 0.000 claims description 8
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 8
229910052702 rhenium Inorganic materials 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
GZPHYSKJSPVVLY-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound C1CNCCC2=NC(N)=NC(N)=C21 GZPHYSKJSPVVLY-UHFFFAOYSA-N 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 claims description 7
229940124530 sulfonamide Drugs 0.000 claims description 7
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
FJNLCHNQVJVCPY-UHFFFAOYSA-N 2-n-methoxy-2-n-methyl-4-n,6-n-dipropyl-1,3,5-triazine-2,4,6-triamine Chemical compound CCCNC1=NC(NCCC)=NC(N(C)OC)=N1 FJNLCHNQVJVCPY-UHFFFAOYSA-N 0.000 claims description 5
PJSSMWNWPZVCKF-UHFFFAOYSA-N 4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoic acid Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(O)=O)C=C1 PJSSMWNWPZVCKF-UHFFFAOYSA-N 0.000 claims description 5
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 5
125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 5
125000005587 carbonate group Chemical group 0.000 claims description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims description 5
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
HMUBBJKULCRYGA-UHFFFAOYSA-N 1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 HMUBBJKULCRYGA-UHFFFAOYSA-N 0.000 claims description 4
UDNZTEXGRXCKEV-UHFFFAOYSA-N 2-morpholin-4-yl-n-(4-piperazin-1-ylsulfonylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)S(=O)(=O)N3CCNCC3)N=C(N3CCOCC3)N=C2CC1 UDNZTEXGRXCKEV-UHFFFAOYSA-N 0.000 claims description 4
FQMKFUBGEBQDJP-UHFFFAOYSA-N 4-[6-(trifluoromethyl)pyridin-3-yl]-1,5,6,7,8,9-hexahydropyrimido[4,5-d]azepine-2,4-diamine Chemical compound N1C(N)=NC(CCNCC2)=C2C1(N)C1=CC=C(C(F)(F)F)N=C1 FQMKFUBGEBQDJP-UHFFFAOYSA-N 0.000 claims description 4
FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical class CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims description 4
229910019142 PO4 Inorganic materials 0.000 claims description 4
125000003725 azepanyl group Chemical group 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 4
125000002843 carboxylic acid group Chemical group 0.000 claims description 4
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 4
125000001033 ether group Chemical group 0.000 claims description 4
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 4
125000005541 phosphonamide group Chemical group 0.000 claims description 4
229920001184 polypeptide Chemical group 0.000 claims description 4
102000004196 processed proteins & peptides Human genes 0.000 claims description 4
108090000765 processed proteins & peptides Chemical group 0.000 claims description 4
WIRTYVGMQVIVDM-UHFFFAOYSA-N pyridine-3-carbonitrile Chemical compound N#CC1=C=NC=C[CH]1 WIRTYVGMQVIVDM-UHFFFAOYSA-N 0.000 claims description 4
150000003456 sulfonamides Chemical class 0.000 claims description 4
LGWBJVHRUMLBHF-UHFFFAOYSA-N 1,1,1-trifluoro-2-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C(C)(O)C(F)(F)F)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 LGWBJVHRUMLBHF-UHFFFAOYSA-N 0.000 claims description 3
MIFDFTQWWHTZML-UHFFFAOYSA-N 1,1,1-trifluoro-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 MIFDFTQWWHTZML-UHFFFAOYSA-N 0.000 claims description 3
KJLDYAUSTGUVRM-UHFFFAOYSA-N 1-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropan-1-ol Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C2(O)CC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 KJLDYAUSTGUVRM-UHFFFAOYSA-N 0.000 claims description 3
JMWQSUOFIBHGAF-UHFFFAOYSA-N 1-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C2(CC2)C(O)=O)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 JMWQSUOFIBHGAF-UHFFFAOYSA-N 0.000 claims description 3
MVLVADGGJYDHKR-UHFFFAOYSA-N 1-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropan-1-ol Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCOCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(O)CC1 MVLVADGGJYDHKR-UHFFFAOYSA-N 0.000 claims description 3
XSDPVSHGOBMVLU-UHFFFAOYSA-N 1-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 XSDPVSHGOBMVLU-UHFFFAOYSA-N 0.000 claims description 3
CXHWWWMUEVGEPY-UHFFFAOYSA-N 1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropan-1-ol Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(O)CC1 CXHWWWMUEVGEPY-UHFFFAOYSA-N 0.000 claims description 3
PIFOWCNRURUNHJ-UHFFFAOYSA-N 1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)O)CC1 PIFOWCNRURUNHJ-UHFFFAOYSA-N 0.000 claims description 3
JWFHVHHGIWNMNV-UHFFFAOYSA-N 1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropan-1-ol Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1C1(O)CC1 JWFHVHHGIWNMNV-UHFFFAOYSA-N 0.000 claims description 3
XANFWSGGNOLZBW-UHFFFAOYSA-N 1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylic acid Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1C1(C(O)=O)CC1 XANFWSGGNOLZBW-UHFFFAOYSA-N 0.000 claims description 3
MZZHVNCJSLWLPA-UHFFFAOYSA-N 1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]ethanol Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)O)C=C1 MZZHVNCJSLWLPA-UHFFFAOYSA-N 0.000 claims description 3
VGJPTLZLDPEKGS-UHFFFAOYSA-N 1-[[4-[2-methyl-4-(trifluoromethyl)anilino]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]sulfanyl]propan-2-ol Chemical compound N=1C(SCC(O)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1C VGJPTLZLDPEKGS-UHFFFAOYSA-N 0.000 claims description 3
FULRIAZHJIQCHL-UHFFFAOYSA-N 1-[[7-[3-(trifluoromethyl)pyridin-2-yl]-4-[(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)amino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]sulfanyl]propan-2-ol Chemical compound C1CC=2C(NC=3C=C4C(C(CCN4C)(C)C)=CC=3)=NC(SCC(O)C)=NC=2CCN1C1=NC=CC=C1C(F)(F)F FULRIAZHJIQCHL-UHFFFAOYSA-N 0.000 claims description 3
YDQHGFVEKWRXFO-UHFFFAOYSA-N 2,2,2-trifluoro-1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]ethanol Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(O)C(F)(F)F)C=C1 YDQHGFVEKWRXFO-UHFFFAOYSA-N 0.000 claims description 3
MQXTYEBBIPGPIY-UHFFFAOYSA-N 2-(furan-2-yl)-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(C=2OC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 MQXTYEBBIPGPIY-UHFFFAOYSA-N 0.000 claims description 3
MKQRPPKJPWCCIS-UHFFFAOYSA-N 2-(furan-3-yl)-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(C2=COC=C2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 MKQRPPKJPWCCIS-UHFFFAOYSA-N 0.000 claims description 3
HRPICFUCYRIBBH-UHFFFAOYSA-N 2-N-(2-methoxyethyl)-2-methyl-7-[3-(trifluoromethyl)pyridin-2-yl]-4-N-[5-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=NC=C(C=C1)C(F)(F)F)NCCOC HRPICFUCYRIBBH-UHFFFAOYSA-N 0.000 claims description 3
JDOGESKAFWIFIE-UHFFFAOYSA-N 2-[2-fluoro-4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=C(F)C(C(C)(O)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 JDOGESKAFWIFIE-UHFFFAOYSA-N 0.000 claims description 3
BYVNAWLJSOMEIQ-UHFFFAOYSA-N 2-[2-fluoro-4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=C(F)C(C(C)(O)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 BYVNAWLJSOMEIQ-UHFFFAOYSA-N 0.000 claims description 3
SENDDIPZFAVZNJ-UHFFFAOYSA-N 2-[4-[[2-(azepan-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 SENDDIPZFAVZNJ-UHFFFAOYSA-N 0.000 claims description 3
KKICAXULBIYBLY-UHFFFAOYSA-N 2-[4-[[2-(azetidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(N2CCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 KKICAXULBIYBLY-UHFFFAOYSA-N 0.000 claims description 3
XFHVQJIZVSRSCY-UHFFFAOYSA-N 2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 XFHVQJIZVSRSCY-UHFFFAOYSA-N 0.000 claims description 3
RMKJRBWZKAQVNJ-UHFFFAOYSA-N 2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 RMKJRBWZKAQVNJ-UHFFFAOYSA-N 0.000 claims description 3
SGAZTJFHHOGHJY-GOSISDBHSA-N 2-[[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound O1C(C)(C)OC[C@H]1COC(N=C1NC=2C=CC(=CC=2)C(F)(F)F)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 SGAZTJFHHOGHJY-GOSISDBHSA-N 0.000 claims description 3
NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
ODDLRJCZVKJKPQ-UHFFFAOYSA-N 2-fluoro-4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoic acid Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(O)=O)C(F)=C1 ODDLRJCZVKJKPQ-UHFFFAOYSA-N 0.000 claims description 3
CTVIAGBZVBVJBA-UHFFFAOYSA-N 2-methyl-2-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanenitrile Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C(C)(C)C#N)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 CTVIAGBZVBVJBA-UHFFFAOYSA-N 0.000 claims description 3
CDAJKKIAIDYBAL-UHFFFAOYSA-N 2-methyl-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 CDAJKKIAIDYBAL-UHFFFAOYSA-N 0.000 claims description 3
RGRQLYKKWNCEIR-UHFFFAOYSA-N 2-methyl-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C(N)=O)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 RGRQLYKKWNCEIR-UHFFFAOYSA-N 0.000 claims description 3
OEFUXFGUSUQBHB-UHFFFAOYSA-N 2-methyl-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanenitrile Chemical compound C1=CC(C(C)(C#N)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 OEFUXFGUSUQBHB-UHFFFAOYSA-N 0.000 claims description 3
UVIIAVDBGUZZMG-UHFFFAOYSA-N 2-methyl-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 UVIIAVDBGUZZMG-UHFFFAOYSA-N 0.000 claims description 3
LNVDMVMPFFDPMA-UHFFFAOYSA-N 2-methyl-2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanenitrile Chemical compound C1=CC(C(C)(C#N)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 LNVDMVMPFFDPMA-UHFFFAOYSA-N 0.000 claims description 3
WAEKLKAUACGKCX-UHFFFAOYSA-N 2-methyl-2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanoic acid Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C(O)=O)C=C1 WAEKLKAUACGKCX-UHFFFAOYSA-N 0.000 claims description 3
XBBYMTFWOSFYRN-UHFFFAOYSA-N 2-methylsulfonyl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=C2N(C)CCC(C)(C)C2=CC=C1NC(C=1CC2)=NC(S(C)(=O)=O)=NC=1CCN2C1=NC=CC=C1C(F)(F)F XBBYMTFWOSFYRN-UHFFFAOYSA-N 0.000 claims description 3
AZJUYRRHHSCDJE-UHFFFAOYSA-N 2-propan-2-yl-n-(4-propan-2-ylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)C)=CC=C1NC1=NC(C(C)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 AZJUYRRHHSCDJE-UHFFFAOYSA-N 0.000 claims description 3
RVTWSZCNDNZGLF-UHFFFAOYSA-N 2-pyrrolidin-1-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 RVTWSZCNDNZGLF-UHFFFAOYSA-N 0.000 claims description 3
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 3
DYSTZSCYZCNRMY-UHFFFAOYSA-N 4-n-[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]benzene-1,4-diamine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(N)C=C1 DYSTZSCYZCNRMY-UHFFFAOYSA-N 0.000 claims description 3
BUDFGQOILPIZOH-UHFFFAOYSA-N 7-(3-fluoropyridin-2-yl)-n-[4-(trifluoromethyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(F)(F)F)N=CN=C2CC1 BUDFGQOILPIZOH-UHFFFAOYSA-N 0.000 claims description 3
JSEUXWZWOZXTJO-UHFFFAOYSA-N 7-[5-amino-3-(trifluoromethyl)pyridin-2-yl]-n-(4-tert-butylphenyl)-2-propan-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC(N)=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 JSEUXWZWOZXTJO-UHFFFAOYSA-N 0.000 claims description 3
XXAFHXLCLGJLHM-SFHVURJKSA-N [(2s)-1-[4-[4-(trifluoromethyl)anilino]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1C(N=C1NC=2C=CC(=CC=2)C(F)(F)F)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 XXAFHXLCLGJLHM-SFHVURJKSA-N 0.000 claims description 3
AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical group NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims description 3
OOKJRFRSPDVVFA-UHFFFAOYSA-N [1-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropyl]methanol Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCOCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(CO)CC1 OOKJRFRSPDVVFA-UHFFFAOYSA-N 0.000 claims description 3
IUEXJBOPXCKEPD-UHFFFAOYSA-N [1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropyl]methanol Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(CO)CC1 IUEXJBOPXCKEPD-UHFFFAOYSA-N 0.000 claims description 3
YEJAJYAHJQIWNU-UHFFFAOYSA-N azelastine hydrochloride Chemical compound Cl.C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YEJAJYAHJQIWNU-UHFFFAOYSA-N 0.000 claims description 3
125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
RMCCUPNQCZTETF-UHFFFAOYSA-N methyl 1-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCOCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)OC)CC1 RMCCUPNQCZTETF-UHFFFAOYSA-N 0.000 claims description 3
UTAJQWLLKTWBGU-UHFFFAOYSA-N methyl 2-methyl-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanoate Chemical compound C1=CC(C(C)(C)C(=O)OC)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 UTAJQWLLKTWBGU-UHFFFAOYSA-N 0.000 claims description 3
GCBKCRNQMCIQID-UHFFFAOYSA-N methyl 2-methyl-2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanoate Chemical compound C1=CC(C(C)(C)C(=O)OC)=CC=C1NC1=NC(C(C)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 GCBKCRNQMCIQID-UHFFFAOYSA-N 0.000 claims description 3
BLMQFMXDWWRNER-UHFFFAOYSA-N n,2-dimethyl-2-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C)C(=O)NC)=CC=C1NC1=NC(N2C(CCC2)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 BLMQFMXDWWRNER-UHFFFAOYSA-N 0.000 claims description 3
FPYQMNSVXGHKJO-UHFFFAOYSA-N n,2-dimethyl-2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C)C(=O)NC)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 FPYQMNSVXGHKJO-UHFFFAOYSA-N 0.000 claims description 3
JLRSQYYWRRJBLJ-UHFFFAOYSA-N n,2-dimethyl-2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C)C(=O)NC)=CC=C1NC1=NC(C(C)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 JLRSQYYWRRJBLJ-UHFFFAOYSA-N 0.000 claims description 3
PNEWKXQRCVHIAP-UHFFFAOYSA-N n,n,2-trimethyl-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C)C(=O)N(C)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 PNEWKXQRCVHIAP-UHFFFAOYSA-N 0.000 claims description 3
DZITUUJODNFHBA-UHFFFAOYSA-N n,n,2-trimethyl-2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C)C(=O)N(C)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 DZITUUJODNFHBA-UHFFFAOYSA-N 0.000 claims description 3
DNUVXHWRVVZLEF-UHFFFAOYSA-N n,n-dimethyl-4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 DNUVXHWRVVZLEF-UHFFFAOYSA-N 0.000 claims description 3
BCUZKAFCUPBWSF-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1C1CCCCC1 BCUZKAFCUPBWSF-UHFFFAOYSA-N 0.000 claims description 3
YFIDVYCUHUJXDD-UHFFFAOYSA-N n-(4-methylsulfonylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(S(C)(=O)=O)C=C1 YFIDVYCUHUJXDD-UHFFFAOYSA-N 0.000 claims description 3
WPCVIVAXGUHEIM-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1N1CCOCC1 WPCVIVAXGUHEIM-UHFFFAOYSA-N 0.000 claims description 3
MKDQTVKDVNZHJG-UHFFFAOYSA-N n-(4-nitrophenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C([N+]([O-])=O)C=C1 MKDQTVKDVNZHJG-UHFFFAOYSA-N 0.000 claims description 3
JYOKLXJCQLUWER-UHFFFAOYSA-N n-(4-piperidin-1-ylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1N1CCCCC1 JYOKLXJCQLUWER-UHFFFAOYSA-N 0.000 claims description 3
KNJTWSLSHAXGKJ-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-cyclopropyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(C2CC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 KNJTWSLSHAXGKJ-UHFFFAOYSA-N 0.000 claims description 3
CSCWLSHCRJKZQR-UHFFFAOYSA-N n-(5-methylpyrazin-2-yl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CN=C(C)C=N1 CSCWLSHCRJKZQR-UHFFFAOYSA-N 0.000 claims description 3
DHWAKOISGIYUBM-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NCC1=CC=CC=C1Cl DHWAKOISGIYUBM-UHFFFAOYSA-N 0.000 claims description 3
FUULNZMAUZTJKB-UHFFFAOYSA-N n-[2-(2-bromophenyl)ethyl]-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NCCC1=CC=CC=C1Br FUULNZMAUZTJKB-UHFFFAOYSA-N 0.000 claims description 3
OACCBZNRMWJWML-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NCCC1=CC=CC(Cl)=C1 OACCBZNRMWJWML-UHFFFAOYSA-N 0.000 claims description 3
PYBVWNBMFHNRPG-UHFFFAOYSA-N n-[2-fluoro-4-(trifluoromethyl)phenyl]-2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 PYBVWNBMFHNRPG-UHFFFAOYSA-N 0.000 claims description 3
HSXSQLHUTDJCHN-UHFFFAOYSA-N n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 HSXSQLHUTDJCHN-UHFFFAOYSA-N 0.000 claims description 3
AIXNQEIKFBISRJ-UHFFFAOYSA-N n-methyl-1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)NC)CC1 AIXNQEIKFBISRJ-UHFFFAOYSA-N 0.000 claims description 3
235000005152 nicotinamide Nutrition 0.000 claims description 3
239000011570 nicotinamide Substances 0.000 claims description 3
DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 3
RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
239000010452 phosphate Substances 0.000 claims description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
STWNGMSGPBZFMX-UHFFFAOYSA-N pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1.NC(=O)C1=CC=CN=C1 STWNGMSGPBZFMX-UHFFFAOYSA-N 0.000 claims description 3
MHRUOIKRPIRMOQ-UHFFFAOYSA-N 1,1,1-trifluoro-2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 MHRUOIKRPIRMOQ-UHFFFAOYSA-N 0.000 claims description 2
125000005962 1,4-oxazepanyl group Chemical group 0.000 claims description 2
WPUQXTYGHWMOAK-UHFFFAOYSA-N 1-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C2(CC2)C(N)=O)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 WPUQXTYGHWMOAK-UHFFFAOYSA-N 0.000 claims description 2
JUPDVMOQYQZLQS-UHFFFAOYSA-N 1-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCOCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)N)CC1 JUPDVMOQYQZLQS-UHFFFAOYSA-N 0.000 claims description 2
RHBJPHKKQZCSEE-UHFFFAOYSA-N 1-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCOCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)O)CC1 RHBJPHKKQZCSEE-UHFFFAOYSA-N 0.000 claims description 2
RNGOXFNYPGCWID-UHFFFAOYSA-N 1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)N)CC1 RNGOXFNYPGCWID-UHFFFAOYSA-N 0.000 claims description 2
PLYQXCLGOXLYQC-UHFFFAOYSA-N 1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1C1(C(N)=O)CC1 PLYQXCLGOXLYQC-UHFFFAOYSA-N 0.000 claims description 2
XOBFFLSBXLOESM-UHFFFAOYSA-N 1-[[4-[4-(trifluoromethyl)anilino]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]sulfanyl]propan-2-ol Chemical compound N=1C(SCC(O)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 XOBFFLSBXLOESM-UHFFFAOYSA-N 0.000 claims description 2
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 2
PISRIIZQRCCCDZ-UHFFFAOYSA-N 2-(2-methoxyethyl)-4-N-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound COCCC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)C(F)(F)F)N PISRIIZQRCCCDZ-UHFFFAOYSA-N 0.000 claims description 2
QRLKSSSLQNLFJL-UHFFFAOYSA-N 2-(azepan-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[5-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 QRLKSSSLQNLFJL-UHFFFAOYSA-N 0.000 claims description 2
ZBTGMECXLABVRA-UHFFFAOYSA-N 2-(azepan-1-yl)-n-[(3,4-dichlorophenyl)methyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCC2=C(NCC=3C=C(Cl)C(Cl)=CC=3)N=C(N3CCCCCC3)N=C2CC1 ZBTGMECXLABVRA-UHFFFAOYSA-N 0.000 claims description 2
PNOABDDUSPYWPY-UHFFFAOYSA-N 2-(cyclohexylmethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-4-N-[6-(trifluoromethyl)pyridin-3-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound C1(CCCCC1)CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC=1C=NC(=CC=1)C(F)(F)F)N PNOABDDUSPYWPY-UHFFFAOYSA-N 0.000 claims description 2
ZOUPYLHDOIUEOZ-UHFFFAOYSA-N 2-(cyclopropylmethyl)-4-N-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound C1(CC1)CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)C(F)(F)F)N ZOUPYLHDOIUEOZ-UHFFFAOYSA-N 0.000 claims description 2
UEQZAQFTQRJMJR-UHFFFAOYSA-N 2-(furan-2-ylmethyl)-2-N-methyl-4-N-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound O1C(=CC=C1)CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)C(F)(F)F)NC UEQZAQFTQRJMJR-UHFFFAOYSA-N 0.000 claims description 2
ZGRYFNJSFBSFCE-UHFFFAOYSA-N 2-N,2-dimethyl-3-(trifluoromethyl)-1H-pyridine-2,6-diamine Chemical compound CC1(NC(=CC=C1C(F)(F)F)N)NC ZGRYFNJSFBSFCE-UHFFFAOYSA-N 0.000 claims description 2
BNMFLFCITXCEAS-FZADBTJQSA-N 2-[(3R)-oxolan-3-yl]-7-[3-(trifluoromethyl)pyridin-2-yl]-4-N-[5-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound O1C[C@H](CC1)C1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=NC=C(C=C1)C(F)(F)F)N BNMFLFCITXCEAS-FZADBTJQSA-N 0.000 claims description 2
WTZKCWZEUNUHNL-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-2-N-methyl-7-[3-(trifluoromethyl)pyridin-2-yl]-4-N-[5-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CN(CCC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=NC=C(C=C1)C(F)(F)F)NC)C WTZKCWZEUNUHNL-UHFFFAOYSA-N 0.000 claims description 2
ZGEMMVUCICYVJS-UHFFFAOYSA-N 2-[2-fluoro-4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)O)C(F)=C1 ZGEMMVUCICYVJS-UHFFFAOYSA-N 0.000 claims description 2
SRLFKTHONBGNEO-UHFFFAOYSA-N 2-[4-[[2-(dimethylamino)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]-2-methylpropanenitrile Chemical compound N=1C(N(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C#N)C=C1 SRLFKTHONBGNEO-UHFFFAOYSA-N 0.000 claims description 2
PEOVLIQUGFAOKG-UHFFFAOYSA-N 2-[4-[[2-(methoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]-2-methylpropanenitrile Chemical compound N=1C(COC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C#N)C=C1 PEOVLIQUGFAOKG-UHFFFAOYSA-N 0.000 claims description 2
YXPGQFFHWAYXLS-UHFFFAOYSA-N 2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)O)C=C1 YXPGQFFHWAYXLS-UHFFFAOYSA-N 0.000 claims description 2
BSBCGIVRJSNJPC-UHFFFAOYSA-N 2-fluoro-4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoic acid Chemical compound CC1CCCN1C(N=C1NC=2C=C(F)C(C(O)=O)=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 BSBCGIVRJSNJPC-UHFFFAOYSA-N 0.000 claims description 2
DQSTZISYQPFYRU-UHFFFAOYSA-N 2-methyl-2-N-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-4-N-[6-(trifluoromethyl)pyridin-3-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC=1C=NC(=CC=1)C(F)(F)F)NC(C)C DQSTZISYQPFYRU-UHFFFAOYSA-N 0.000 claims description 2
PUPMVDKUNMKHOW-UHFFFAOYSA-N 2-methyl-2-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-1-ol Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C(C)(C)CO)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 PUPMVDKUNMKHOW-UHFFFAOYSA-N 0.000 claims description 2
PKBPUKYDLDGPQR-UHFFFAOYSA-N 2-methyl-2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 PKBPUKYDLDGPQR-UHFFFAOYSA-N 0.000 claims description 2
HXFLMTHANHQLCY-UHFFFAOYSA-N 2-methyl-2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C(N)=O)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 HXFLMTHANHQLCY-UHFFFAOYSA-N 0.000 claims description 2
MTRRARFCGONWPC-UHFFFAOYSA-N 2-methyl-2-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 MTRRARFCGONWPC-UHFFFAOYSA-N 0.000 claims description 2
XAYLPRQRLQTXIZ-UHFFFAOYSA-N 2-methyl-2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C(N)=O)C=C1 XAYLPRQRLQTXIZ-UHFFFAOYSA-N 0.000 claims description 2
ULBIQHDQWCAKFT-UHFFFAOYSA-N 2-methylsulfanyl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1CC=2C(NC=3C=C4C(C(CCN4C)(C)C)=CC=3)=NC(SC)=NC=2CCN1C1=NC=CC=C1C(F)(F)F ULBIQHDQWCAKFT-UHFFFAOYSA-N 0.000 claims description 2
WDSQKQFNGIKBHH-UHFFFAOYSA-N 2-morpholin-4-yl-n-(4-morpholin-4-ylsulfonylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)S(=O)(=O)N3CCOCC3)N=C(N3CCOCC3)N=C2CC1 WDSQKQFNGIKBHH-UHFFFAOYSA-N 0.000 claims description 2
IWMQFVDKTVOCLP-UHFFFAOYSA-N 2-phenylsulfanyl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(SC=2C=CC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 IWMQFVDKTVOCLP-UHFFFAOYSA-N 0.000 claims description 2
LMPHSOGPKNZCDE-UHFFFAOYSA-N 2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=C2N(C)CCC(C)(C)C2=CC=C1NC(C=1CC2)=NC(N3CCCCC3)=NC=1CCN2C1=NC=CC=C1C(F)(F)F LMPHSOGPKNZCDE-UHFFFAOYSA-N 0.000 claims description 2
LWPDBEDFDMJWGZ-UHFFFAOYSA-N 2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[4-(trifluoromethylsulfanyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(SC(F)(F)F)C=C1 LWPDBEDFDMJWGZ-UHFFFAOYSA-N 0.000 claims description 2
VWGFVSAZQNJDQW-UHFFFAOYSA-N 2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[4-(trifluoromethylsulfonyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 VWGFVSAZQNJDQW-UHFFFAOYSA-N 0.000 claims description 2
HVVGINLQYJFFDY-UHFFFAOYSA-N 2-propan-2-yl-n-[4-(trifluoromethoxy)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(OC(F)(F)F)C=C1 HVVGINLQYJFFDY-UHFFFAOYSA-N 0.000 claims description 2
JLUPPDDCRBRIEI-UHFFFAOYSA-N 2-thiophen-3-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(C2=CSC=C2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 JLUPPDDCRBRIEI-UHFFFAOYSA-N 0.000 claims description 2
UWHHLMOMANLMRU-UHFFFAOYSA-N 4-N-(4-tert-butylphenyl)-2-[2-(dimethylamino)ethyl]-2-N-methyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CN(CCC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)C(C)(C)C)NC)C UWHHLMOMANLMRU-UHFFFAOYSA-N 0.000 claims description 2
QSCNGGNYGUCHSX-UHFFFAOYSA-N 4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 QSCNGGNYGUCHSX-UHFFFAOYSA-N 0.000 claims description 2
DQWKVFSMFBCRDI-UHFFFAOYSA-N 4-tert-butyl-1-n-[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]benzene-1,3-diamine Chemical compound C1=C(N)C(C(C)(C)C)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 DQWKVFSMFBCRDI-UHFFFAOYSA-N 0.000 claims description 2
ZAKRQXFSYHWQIR-UHFFFAOYSA-N 4-tert-butyl-1-n-[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]benzene-1,3-diamine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C)C(N)=C1 ZAKRQXFSYHWQIR-UHFFFAOYSA-N 0.000 claims description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
XXAFHXLCLGJLHM-GOSISDBHSA-N [(2r)-1-[4-[4-(trifluoromethyl)anilino]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@H]1CCCN1C(N=C1NC=2C=CC(=CC=2)C(F)(F)F)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 XXAFHXLCLGJLHM-GOSISDBHSA-N 0.000 claims description 2
AGSWHNKJQMZXBO-UHFFFAOYSA-N [1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropyl]methanol Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1C1(CO)CC1 AGSWHNKJQMZXBO-UHFFFAOYSA-N 0.000 claims description 2
ZFHPXSRPNQRBCM-UHFFFAOYSA-N [4-[4-[2-methyl-4-(trifluoromethyl)anilino]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]morpholin-2-yl]methanol Chemical compound CC1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CC(CO)OCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 ZFHPXSRPNQRBCM-UHFFFAOYSA-N 0.000 claims description 2
WFOHHQXMVNVTQL-UHFFFAOYSA-N [5-chloro-6-[2-piperidin-1-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridin-3-yl]methanol Chemical compound ClC1=CC(CO)=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(F)(F)F)N=C(N3CCCCC3)N=C2CC1 WFOHHQXMVNVTQL-UHFFFAOYSA-N 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
PYCOETNUJFMYPX-UHFFFAOYSA-N methyl 1-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2C(CCC2)C)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)OC)CC1 PYCOETNUJFMYPX-UHFFFAOYSA-N 0.000 claims description 2
LEAUTMAXJCVAPB-UHFFFAOYSA-N methyl 1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)OC)CC1 LEAUTMAXJCVAPB-UHFFFAOYSA-N 0.000 claims description 2
GKHWMFFRKUIPHL-UHFFFAOYSA-N methyl 1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)C(C)C)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)OC)CC1 GKHWMFFRKUIPHL-UHFFFAOYSA-N 0.000 claims description 2
GTSJYTLUTGETKL-UHFFFAOYSA-N methyl 4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 GTSJYTLUTGETKL-UHFFFAOYSA-N 0.000 claims description 2
MPUWZVZMKAKURZ-UHFFFAOYSA-N methyl 4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 MPUWZVZMKAKURZ-UHFFFAOYSA-N 0.000 claims description 2
SNSPFVJWZAGRBI-UHFFFAOYSA-N methyl 5-chloro-6-[2-methylsulfanyl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridine-3-carboxylate Chemical compound ClC1=CC(C(=O)OC)=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(F)(F)F)N=C(SC)N=C2CC1 SNSPFVJWZAGRBI-UHFFFAOYSA-N 0.000 claims description 2
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 2
LMFPLWOYLQEOTM-UHFFFAOYSA-N n,2-dimethyl-2-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound C1=CC(C(C)(C)C(=O)NC)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 LMFPLWOYLQEOTM-UHFFFAOYSA-N 0.000 claims description 2
WGQONVPFJXLGJG-UHFFFAOYSA-N n,n,2-trimethyl-2-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C(C)(C)C(=O)N(C)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 WGQONVPFJXLGJG-UHFFFAOYSA-N 0.000 claims description 2
SPYKOKJZRQXBQT-UHFFFAOYSA-N n,n,2-trimethyl-2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C(=O)N(C)C)C=C1 SPYKOKJZRQXBQT-UHFFFAOYSA-N 0.000 claims description 2
ZTLJHNVIUAEPTA-UHFFFAOYSA-N n,n-dimethyl-1-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C2(CC2)C(=O)N(C)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 ZTLJHNVIUAEPTA-UHFFFAOYSA-N 0.000 claims description 2
MZPXWZMUBHUYPU-UHFFFAOYSA-N n,n-dimethyl-1-[4-[[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)N(C)C)CC1 MZPXWZMUBHUYPU-UHFFFAOYSA-N 0.000 claims description 2
FJJUUDSNFIKAPH-UHFFFAOYSA-N n,n-dimethyl-4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzenesulfonamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(S(=O)(=O)N(C)C)C=C1 FJJUUDSNFIKAPH-UHFFFAOYSA-N 0.000 claims description 2
KCMIXDAAGDQBDI-UHFFFAOYSA-N n-(4-bromophenyl)-2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound CC1CCCN1C(N=C1NC=2C=CC(Br)=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 KCMIXDAAGDQBDI-UHFFFAOYSA-N 0.000 claims description 2
YTJCKQRSCBUBPB-UHFFFAOYSA-N n-(4-chlorophenyl)-2-cyclopropyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(Cl)=CC=3)N=C(C3CC3)N=C2CC1 YTJCKQRSCBUBPB-UHFFFAOYSA-N 0.000 claims description 2
WVVYXMJDFDYYKA-UHFFFAOYSA-N n-(4-methylsulfanylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(SC)=CC=C1NC1=NC(C(C)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 WVVYXMJDFDYYKA-UHFFFAOYSA-N 0.000 claims description 2
AMEOEEKSHBWAQN-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-pyridin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(C=2C=CN=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 AMEOEEKSHBWAQN-UHFFFAOYSA-N 0.000 claims description 2
AWDFZCVZVPLLAI-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-methylsulfanyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(SC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NCC1=CC=C(Cl)C(Cl)=C1 AWDFZCVZVPLLAI-UHFFFAOYSA-N 0.000 claims description 2
WTMRTCFXRGNTCE-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)ethyl]-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NCCC1=CC=C(Cl)C(Cl)=C1 WTMRTCFXRGNTCE-UHFFFAOYSA-N 0.000 claims description 2
VCIDLFZYHBUOJH-UHFFFAOYSA-N n-[2-[2-propan-2-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]phenyl]methanesulfonamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CC=3)NS(C)(=O)=O)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 VCIDLFZYHBUOJH-UHFFFAOYSA-N 0.000 claims description 2
YKZGDXYKEQTAFA-UHFFFAOYSA-N n-[3-chloro-4-(trifluoromethyl)phenyl]-2-pyridin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC=C1NC1=NC(C=2C=CN=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 YKZGDXYKEQTAFA-UHFFFAOYSA-N 0.000 claims description 2
FITOVOKPNAZBOF-UHFFFAOYSA-N n-[4-[1-(aminomethyl)cyclopropyl]phenyl]-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1C1(CN)CC1 FITOVOKPNAZBOF-UHFFFAOYSA-N 0.000 claims description 2
FOTRKXNICOZQHV-UHFFFAOYSA-N n-[6-methoxy-5-(trifluoromethyl)pyridin-2-yl]-2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=C(C(F)(F)F)C(OC)=NC(NC=2C=3CCN(CCC=3N=C(N=2)N2CCOCC2)C=2C(=CC=CN=2)C(F)(F)F)=C1 FOTRKXNICOZQHV-UHFFFAOYSA-N 0.000 claims description 2
COKOGXCQUPTSMY-UHFFFAOYSA-N n-[6-methoxy-5-(trifluoromethyl)pyridin-2-yl]-2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=C(C(F)(F)F)C(OC)=NC(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)=C1 COKOGXCQUPTSMY-UHFFFAOYSA-N 0.000 claims description 2
DSDXDQQNKNDVEP-UHFFFAOYSA-N n-methyl-1-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2C(CCC2)C)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)NC)CC1 DSDXDQQNKNDVEP-UHFFFAOYSA-N 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims 4
UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 claims 4
JPYQYVBZLSMDEY-UHFFFAOYSA-N n-[2-[2-propan-2-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridin-3-yl]methanesulfonamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)NS(C)(=O)=O)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 JPYQYVBZLSMDEY-UHFFFAOYSA-N 0.000 claims 3
OIDRTSZUTJPZOG-UHFFFAOYSA-N 2-(azepan-1-yl)-n-(4-tert-butylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 OIDRTSZUTJPZOG-UHFFFAOYSA-N 0.000 claims 2
XYQNDDZYDIMAPD-UHFFFAOYSA-N 2-(azepan-1-yl)-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 XYQNDDZYDIMAPD-UHFFFAOYSA-N 0.000 claims 2
XGNCNBHIVRKPJN-UHFFFAOYSA-N 2-N-[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]-3-(trifluoromethyl)pyridine-2,6-diamine Chemical compound C(C)(C)C=1N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=NC(=CC=C1C(F)(F)F)N XGNCNBHIVRKPJN-UHFFFAOYSA-N 0.000 claims 2
LJSAEIXAKVLJNT-UHFFFAOYSA-N 2-[2-fluoro-4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound CC1CCCN1C(N=C1NC=2C=C(F)C(=CC=2)C(C)(C)O)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 LJSAEIXAKVLJNT-UHFFFAOYSA-N 0.000 claims 2
VXBXFGLJWHFFOI-UHFFFAOYSA-N 2-[2-piperidin-1-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]-n-propan-2-ylpyridine-3-sulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(F)(F)F)N=C(N3CCCCC3)N=C2CC1 VXBXFGLJWHFFOI-UHFFFAOYSA-N 0.000 claims 2
GXWKCQMNBIBIAL-UHFFFAOYSA-N 2-methyl-2-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanamide Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C(C)(C)C(N)=O)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 GXWKCQMNBIBIAL-UHFFFAOYSA-N 0.000 claims 2
CPISAMSADQLHIT-UHFFFAOYSA-N 2-methyl-3-(trifluoromethyl)-1H-pyridine-2,6-diamine Chemical compound CC1(NC(=CC=C1C(F)(F)F)N)N CPISAMSADQLHIT-UHFFFAOYSA-N 0.000 claims 2
MZGUCZKVMGOWMO-UHFFFAOYSA-N 2-methylsulfanyl-7-(3-methylsulfonylpyridin-2-yl)-n-[4-(trifluoromethyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(SC)=NC=2CCN(C=3C(=CC=CN=3)S(C)(=O)=O)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 MZGUCZKVMGOWMO-UHFFFAOYSA-N 0.000 claims 2
VXMBPOXBOYZLMH-UHFFFAOYSA-N 2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1CC=2C(NC=3C=C4C(C(CCN4C)(C)C)=CC=3)=NC(C(C)C)=NC=2CCN1C1=NC=CC=C1C(F)(F)F VXMBPOXBOYZLMH-UHFFFAOYSA-N 0.000 claims 2
DTVDJTKZWIYBES-UHFFFAOYSA-N 2-propan-2-yl-n-pyrimidin-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=NC=CC=N1 DTVDJTKZWIYBES-UHFFFAOYSA-N 0.000 claims 2
HTUVWWLYSOYLAR-UHFFFAOYSA-N 2-pyridin-4-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(C=2C=CN=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 HTUVWWLYSOYLAR-UHFFFAOYSA-N 0.000 claims 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
KZZSAHWCIIETDZ-UHFFFAOYSA-N 4-[3-chloro-4-(trifluoromethyl)phenyl]-2-N-[2-(dimethylamino)ethyl]-2-N-methyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound ClC=1C=C(C=CC=1C(F)(F)F)C1(NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N(C)CCN(C)C)N KZZSAHWCIIETDZ-UHFFFAOYSA-N 0.000 claims 2
JTUMZYDIRDVQCC-UHFFFAOYSA-N 7-(3-aminopyridin-2-yl)-n-(4-tert-butylphenyl)-2-propan-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)N)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 JTUMZYDIRDVQCC-UHFFFAOYSA-N 0.000 claims 2
QQEQEUKNJBHKEX-UHFFFAOYSA-N 7-(3-ethylsulfonylpyridin-2-yl)-2-piperidin-1-yl-n-[4-(trifluoromethyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound CCS(=O)(=O)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(F)(F)F)N=C(N3CCCCC3)N=C2CC1 QQEQEUKNJBHKEX-UHFFFAOYSA-N 0.000 claims 2
JEFNXJBWGVEHMM-UHFFFAOYSA-N 7-(5-bromo-3-chloropyridin-2-yl)-n-(4-tert-butylphenyl)-2-propan-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC(Br)=CN=3)Cl)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 JEFNXJBWGVEHMM-UHFFFAOYSA-N 0.000 claims 2
XSBPINPHYDAMMW-UHFFFAOYSA-N CN(CCOC)C1=NC(C2=C(N1)CCN(CC2)C3=C(C=CC=N3)C(F)(F)F)(CC4=CC(=C(C=C4)Cl)Cl)N Chemical compound CN(CCOC)C1=NC(C2=C(N1)CCN(CC2)C3=C(C=CC=N3)C(F)(F)F)(CC4=CC(=C(C=C4)Cl)Cl)N XSBPINPHYDAMMW-UHFFFAOYSA-N 0.000 claims 2
NTOYDKHNSJJIQM-UHFFFAOYSA-N [1-[4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropyl]methanol Chemical compound CC1CCCN1C(N=C1NC=2C=CC(=CC=2)C2(CO)CC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 NTOYDKHNSJJIQM-UHFFFAOYSA-N 0.000 claims 2
ANHZBUMWGGAWDL-UHFFFAOYSA-N [5-chloro-6-[2-methylsulfanyl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridin-3-yl]methanol Chemical compound N=1C(SC)=NC=2CCN(C=3C(=CC(CO)=CN=3)Cl)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 ANHZBUMWGGAWDL-UHFFFAOYSA-N 0.000 claims 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
ZZSJKJSXOFQQTO-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(Cl)C(Cl)=C1 ZZSJKJSXOFQQTO-UHFFFAOYSA-N 0.000 claims 2
RKJICNPHSPMDBR-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(furan-2-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(C=2OC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 RKJICNPHSPMDBR-UHFFFAOYSA-N 0.000 claims 2
XJROGCFXTSDZAN-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(furan-3-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(C2=COC=C2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 XJROGCFXTSDZAN-UHFFFAOYSA-N 0.000 claims 2
HUWDXCSRDAPMOC-UHFFFAOYSA-N n-(4-tert-butylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 HUWDXCSRDAPMOC-UHFFFAOYSA-N 0.000 claims 2
DWAMESVAXZGQSZ-UHFFFAOYSA-N n-(4-tert-butylphenyl)-7-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-propan-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC(=CN=3)C(F)(F)F)Cl)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 DWAMESVAXZGQSZ-UHFFFAOYSA-N 0.000 claims 2
YMYQTLKJWHBSQK-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NCCC1=CC=C(Cl)C=C1 YMYQTLKJWHBSQK-UHFFFAOYSA-N 0.000 claims 2
RALXVJDONOFEEE-UHFFFAOYSA-N n-[4-(1-amino-2-methylpropan-2-yl)phenyl]-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)CN)C=C1 RALXVJDONOFEEE-UHFFFAOYSA-N 0.000 claims 2
JPHRNZLHGDOFOQ-UHFFFAOYSA-N n-[4-[1-(aminomethyl)cyclopropyl]phenyl]-2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCCCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(CN)CC1 JPHRNZLHGDOFOQ-UHFFFAOYSA-N 0.000 claims 2
KLGSMNZULWYDRI-UHFFFAOYSA-N n-[6-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N1=C(Cl)C(C(F)(F)F)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 KLGSMNZULWYDRI-UHFFFAOYSA-N 0.000 claims 2
FRJOORZORFJVNU-UHFFFAOYSA-N n-methyl-1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)C(C)C)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)NC)CC1 FRJOORZORFJVNU-UHFFFAOYSA-N 0.000 claims 2
RVGXXSOVXGVIJU-UHFFFAOYSA-N 1,1,1-trifluoro-2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(O)C(F)(F)F)C=C1 RVGXXSOVXGVIJU-UHFFFAOYSA-N 0.000 claims 1
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
CJQGAUQGFUJCNK-UHFFFAOYSA-N 2-(2-methyloxolan-3-yl)sulfanyl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[4-(trifluoromethylsulfonyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound CC1OCCC1SC(N=C1NC=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 CJQGAUQGFUJCNK-UHFFFAOYSA-N 0.000 claims 1
AOSKXJDFJABASI-UHFFFAOYSA-N 2-(2-piperidin-1-ylethyl)-4-N-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound N1(CCCCC1)CCC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)C(F)(F)F)N AOSKXJDFJABASI-UHFFFAOYSA-N 0.000 claims 1
DSSSQPCOLCZONG-UHFFFAOYSA-N 2-(azepan-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[6-(trifluoromethyl)pyridin-3-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=NC(C(F)(F)F)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 DSSSQPCOLCZONG-UHFFFAOYSA-N 0.000 claims 1
PHZRFTAWXVMMJG-UHFFFAOYSA-N 2-(azetidin-1-yl)-n-(4-tert-butylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(N2CCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 PHZRFTAWXVMMJG-UHFFFAOYSA-N 0.000 claims 1
XSJOKQIPEFOWGV-UHFFFAOYSA-N 2-(methoxymethyl)-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(COC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 XSJOKQIPEFOWGV-UHFFFAOYSA-N 0.000 claims 1
FSPJULXJNQOFRZ-UHFFFAOYSA-N 2-(oxan-4-yl)-4-N-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound O1CCC(CC1)C1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)C(F)(F)F)N FSPJULXJNQOFRZ-UHFFFAOYSA-N 0.000 claims 1
DXZWGUWURKGFGY-UHFFFAOYSA-N 2-N,2-dimethyl-4-N-(4-nitrophenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)[N+](=O)[O-])NC DXZWGUWURKGFGY-UHFFFAOYSA-N 0.000 claims 1
CRHHOZBQZRIPRT-UHFFFAOYSA-N 2-N,2-dimethyl-6-N-[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]-3-(trifluoromethyl)-1H-pyridine-2,6-diamine Chemical compound CC1(NC(=CC=C1C(F)(F)F)NC1=NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N1CCOCC1)NC CRHHOZBQZRIPRT-UHFFFAOYSA-N 0.000 claims 1
VYXSRKDMMGYUBQ-UHFFFAOYSA-N 2-N,2-dimethyl-6-N-[2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]-3-(trifluoromethyl)-1H-pyridine-2,6-diamine Chemical compound CC1(NC(=CC=C1C(F)(F)F)NC1=NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N1CCCCC1)NC VYXSRKDMMGYUBQ-UHFFFAOYSA-N 0.000 claims 1
ZRGGKLDPOYLPSV-UHFFFAOYSA-N 2-N-(2-methoxyethyl)-2-methyl-7-[3-(trifluoromethyl)pyridin-2-yl]-4-N-[6-(trifluoromethyl)pyridin-3-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC=1C=NC(=CC=1)C(F)(F)F)NCCOC ZRGGKLDPOYLPSV-UHFFFAOYSA-N 0.000 claims 1
QACPKUVSUOXIMG-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-2-N-methyl-4-N-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CN(CCC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)NC1=CC=C(C=C1)C(F)(F)F)NC)C QACPKUVSUOXIMG-UHFFFAOYSA-N 0.000 claims 1
AKVNOCUPMPFXSQ-UHFFFAOYSA-N 2-[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]-5-(trifluoromethyl)-1H-pyridine-2,6-diamine Chemical compound N1(CCOCC1)C=1N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N=1)C1(C=CC(=C(N1)N)C(F)(F)F)N AKVNOCUPMPFXSQ-UHFFFAOYSA-N 0.000 claims 1
DLYRQZSRSNAJED-UHFFFAOYSA-N 2-[2-piperidin-1-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(F)(F)F)N=C(N3CCCCC3)N=C2CC1 DLYRQZSRSNAJED-UHFFFAOYSA-N 0.000 claims 1
SGAZTJFHHOGHJY-SFHVURJKSA-N 2-[[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound O1C(C)(C)OC[C@@H]1COC(N=C1NC=2C=CC(=CC=2)C(F)(F)F)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 SGAZTJFHHOGHJY-SFHVURJKSA-N 0.000 claims 1
RRELSALQABTEMT-UHFFFAOYSA-N 2-butoxy-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[6-(trifluoromethyl)pyridin-3-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(OCCCC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)N=C1 RRELSALQABTEMT-UHFFFAOYSA-N 0.000 claims 1
HXPVYPCMRHJKMR-UHFFFAOYSA-N 2-ethoxy-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(OCC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 HXPVYPCMRHJKMR-UHFFFAOYSA-N 0.000 claims 1
ASXJDZYEOMQCCU-UHFFFAOYSA-N 2-methyl-2-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propanenitrile Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C#N)C=C1 ASXJDZYEOMQCCU-UHFFFAOYSA-N 0.000 claims 1
FAOGWAGNSHOBLS-UHFFFAOYSA-N 2-methyl-6-N-[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]-3-(trifluoromethyl)-1H-pyridine-2,6-diamine Chemical compound CC1(NC(=CC=C1C(F)(F)F)NC1=NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N1CCOCC1)N FAOGWAGNSHOBLS-UHFFFAOYSA-N 0.000 claims 1
AAKZHSRNJWJRCU-UHFFFAOYSA-N 2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[4-(trifluoromethylsulfonyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)S(=O)(=O)C(F)(F)F)N=C(N3CCOCC3)N=C2CC1 AAKZHSRNJWJRCU-UHFFFAOYSA-N 0.000 claims 1
AQXHHWRBYRCPMW-UHFFFAOYSA-N 2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[6-(trifluoromethyl)pyridin-3-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=NC(C(F)(F)F)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 AQXHHWRBYRCPMW-UHFFFAOYSA-N 0.000 claims 1
FZERIEWDXDEMHS-UHFFFAOYSA-N 2-morpholin-4-yl-n-(4-pyrrolidin-1-ylsulfonylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)S(=O)(=O)N3CCCC3)N=C(N3CCOCC3)N=C2CC1 FZERIEWDXDEMHS-UHFFFAOYSA-N 0.000 claims 1
ISEPAEPQASBPKZ-UHFFFAOYSA-N 2-n-phenyl-4-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepine-2,4-diamine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(NC=2C=CC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 ISEPAEPQASBPKZ-UHFFFAOYSA-N 0.000 claims 1
OCBCQHBSUGOVMB-UHFFFAOYSA-N 2-phenylsulfanyl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=C2N(C)CCC(C)(C)C2=CC=C1NC(C=1CCN(CCC=1N=1)C=2C(=CC=CN=2)C(F)(F)F)=NC=1SC1=CC=CC=C1 OCBCQHBSUGOVMB-UHFFFAOYSA-N 0.000 claims 1
LLFYVTXCWCVAFZ-UHFFFAOYSA-N 2-propan-2-yl-n-(4-pyrrolidin-1-ylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1N1CCCC1 LLFYVTXCWCVAFZ-UHFFFAOYSA-N 0.000 claims 1
IIBXMCJVFSOCFT-UHFFFAOYSA-N 2-propan-2-yl-n-[3-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=CC(C(F)(F)F)=C1 IIBXMCJVFSOCFT-UHFFFAOYSA-N 0.000 claims 1
HGMDWMYRICKNCH-UHFFFAOYSA-N 2-propan-2-yl-n-pyrimidin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=NC=N1 HGMDWMYRICKNCH-UHFFFAOYSA-N 0.000 claims 1
LFPDMRRWUGOGAC-UHFFFAOYSA-N 2-pyridin-2-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(C=2N=CC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 LFPDMRRWUGOGAC-UHFFFAOYSA-N 0.000 claims 1
QWGVOIVLYTUILU-UHFFFAOYSA-N 2-pyridin-3-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(C=2C=NC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 QWGVOIVLYTUILU-UHFFFAOYSA-N 0.000 claims 1
BLXXEJYBIHUAMZ-UHFFFAOYSA-N 2-pyridin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-n-[6-(trifluoromethyl)pyridin-3-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=NC(C(F)(F)F)=CC=C1NC1=NC(C=2C=CN=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 BLXXEJYBIHUAMZ-UHFFFAOYSA-N 0.000 claims 1
YXNVVYPETIRQDG-UHFFFAOYSA-N 2-tert-butyl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 YXNVVYPETIRQDG-UHFFFAOYSA-N 0.000 claims 1
IRHQUHOLXWZCCL-UHFFFAOYSA-N 2-thiophen-2-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(C=2SC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 IRHQUHOLXWZCCL-UHFFFAOYSA-N 0.000 claims 1
UFHVIMSZFPSQSE-UHFFFAOYSA-N 4-(2,3-dihydro-1H-inden-2-yl)-2-N,2-N-dimethyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound C1C(CC2=CC=CC=C12)C1(NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N(C)C)N UFHVIMSZFPSQSE-UHFFFAOYSA-N 0.000 claims 1
HFDDZSNKQXIQPV-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-N,2-N-dimethyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound ClC=1C=C(C=CC=1Cl)C1(NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N(C)C)N HFDDZSNKQXIQPV-UHFFFAOYSA-N 0.000 claims 1
CISZMXAQEZAMJO-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-N,2-N-dimethyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound COC1=CC=C(C=C1)C1(NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N(C)C)N CISZMXAQEZAMJO-UHFFFAOYSA-N 0.000 claims 1
UKCPAMKOABPBEF-UHFFFAOYSA-N 4-[4-methoxy-3-(trifluoromethyl)phenyl]-2-N,2-N-dimethyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound COC1=C(C=C(C=C1)C1(NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N(C)C)N)C(F)(F)F UKCPAMKOABPBEF-UHFFFAOYSA-N 0.000 claims 1
DZDJMMFXQWXXIA-UHFFFAOYSA-N 4-[[2-(dimethylamino)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzonitrile Chemical compound N=1C(N(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C#N)C=C1 DZDJMMFXQWXXIA-UHFFFAOYSA-N 0.000 claims 1
XMOONQRALKFUCK-UHFFFAOYSA-N 4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 XMOONQRALKFUCK-UHFFFAOYSA-N 0.000 claims 1
UDKZDRIYYZZWMB-UHFFFAOYSA-N 4-benzyl-2-N,2-N-dimethyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound C(C1=CC=CC=C1)C1(NC(=NC=2CCN(CCC=21)C1=NC=CC=C1C(F)(F)F)N(C)C)N UDKZDRIYYZZWMB-UHFFFAOYSA-N 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
XUFDWFZCRYPISY-UHFFFAOYSA-N 5-chloro-6-[2-propan-2-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridine-3-carboxylic acid Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC(=CN=3)C(O)=O)Cl)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 XUFDWFZCRYPISY-UHFFFAOYSA-N 0.000 claims 1
KSCRSLIOYGMPNO-UHFFFAOYSA-N 5h-pyrimido[4,5-d]azepin-4-amine Chemical compound C1=CN=CCC2=C1N=CN=C2N KSCRSLIOYGMPNO-UHFFFAOYSA-N 0.000 claims 1
UMDKOTRMUPWALU-UHFFFAOYSA-N 6-N,6-N-dimethyl-2-[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]-5-(trifluoromethyl)-1H-pyridine-2,6-diamine Chemical compound C(C)(C)C=1N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N=1)C1(C=CC(=C(N1)N(C)C)C(F)(F)F)N UMDKOTRMUPWALU-UHFFFAOYSA-N 0.000 claims 1
WTTUTVHQERNVQN-UHFFFAOYSA-N 7-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-propan-2-yl-n-[4-(trifluoromethyl)phenyl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC(=CN=3)C(F)(F)F)Cl)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 WTTUTVHQERNVQN-UHFFFAOYSA-N 0.000 claims 1
NIOIDMCFIJSHKW-UHFFFAOYSA-N C1COCC1C2(NC3=C(CCN(CC3)C4=C(C=CC=N4)C(F)(F)F)C(=N2)NC5=CC=C(C=C5)C(F)(F)F)N Chemical compound C1COCC1C2(NC3=C(CCN(CC3)C4=C(C=CC=N4)C(F)(F)F)C(=N2)NC5=CC=C(C=C5)C(F)(F)F)N NIOIDMCFIJSHKW-UHFFFAOYSA-N 0.000 claims 1
NSYVCEYQLFKRJE-UHFFFAOYSA-N CC1=CC=C(C=C1)C2(NC3=C(CCN(CC3)C4=C(C=CC=N4)C(F)(F)F)C(=N2)NC5=CC=C(C=C5)C(F)(F)F)N Chemical compound CC1=CC=C(C=C1)C2(NC3=C(CCN(CC3)C4=C(C=CC=N4)C(F)(F)F)C(=N2)NC5=CC=C(C=C5)C(F)(F)F)N NSYVCEYQLFKRJE-UHFFFAOYSA-N 0.000 claims 1
DPBYCXOSWQBRHO-UHFFFAOYSA-N CN(CCOC)C1=NC(C2=C(N1)CCN(CC2)C3=C(C=CC=N3)C(F)(F)F)(C4=CC(=C(C=C4)C(F)(F)F)Cl)N Chemical compound CN(CCOC)C1=NC(C2=C(N1)CCN(CC2)C3=C(C=CC=N3)C(F)(F)F)(C4=CC(=C(C=C4)C(F)(F)F)Cl)N DPBYCXOSWQBRHO-UHFFFAOYSA-N 0.000 claims 1
VEBXESWALRZCMT-ZJTJSSCZSA-N [2H]C1=CC=CN=C(C1)[2H] Chemical compound [2H]C1=CC=CN=C(C1)[2H] VEBXESWALRZCMT-ZJTJSSCZSA-N 0.000 claims 1
OIFCGYNNTOHQSG-UHFFFAOYSA-N [4-[4-[4-(trifluoromethyl)anilino]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]morpholin-2-yl]methanol Chemical compound C1COC(CO)CN1C(N=C1NC=2C=CC(=CC=2)C(F)(F)F)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 OIFCGYNNTOHQSG-UHFFFAOYSA-N 0.000 claims 1
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 claims 1
230000000052 comparative effect Effects 0.000 claims 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
NDZTVZYZGFQVLH-UHFFFAOYSA-N methyl 2-fluoro-4-[[2-(2-methylpyrrolidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoate Chemical compound C1=C(F)C(C(=O)OC)=CC=C1NC1=NC(N2C(CCC2)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 NDZTVZYZGFQVLH-UHFFFAOYSA-N 0.000 claims 1
LXANOUTXZXXGRH-UHFFFAOYSA-N methyl 4-[[2-(dimethylamino)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NC(N(C)C)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 LXANOUTXZXXGRH-UHFFFAOYSA-N 0.000 claims 1
ORTJDXCLGNFPIC-UHFFFAOYSA-N methyl 5-chloro-6-[2-piperidin-1-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridine-3-carboxylate Chemical compound ClC1=CC(C(=O)OC)=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(F)(F)F)N=C(N3CCCCC3)N=C2CC1 ORTJDXCLGNFPIC-UHFFFAOYSA-N 0.000 claims 1
LWMWXRBYFMBTJN-UHFFFAOYSA-N n,n-dimethyl-1-[4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC=2C=3CCN(CCC=3N=C(N=2)N2CCOCC2)C=2C(=CC=CN=2)C(F)(F)F)C=CC=1C1(C(=O)N(C)C)CC1 LWMWXRBYFMBTJN-UHFFFAOYSA-N 0.000 claims 1
VBXZFCCNNSNIRY-UHFFFAOYSA-N n,n-dimethyl-4-[[2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=NC(N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 VBXZFCCNNSNIRY-UHFFFAOYSA-N 0.000 claims 1
NFLXCCPMZPRXGG-UHFFFAOYSA-N n-(1-methyl-3,4-dihydro-2h-quinolin-7-yl)-2-morpholin-4-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=C2N(C)CCCC2=CC=C1NC(C=1CC2)=NC(N3CCOCC3)=NC=1CCN2C1=NC=CC=C1C(F)(F)F NFLXCCPMZPRXGG-UHFFFAOYSA-N 0.000 claims 1
RUJMOILXNIBIKF-UHFFFAOYSA-N n-(4-methylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C)C=C1 RUJMOILXNIBIKF-UHFFFAOYSA-N 0.000 claims 1
SRBRGADEBFLEFC-UHFFFAOYSA-N n-(4-methylsulfanylphenyl)-2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(SC)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 SRBRGADEBFLEFC-UHFFFAOYSA-N 0.000 claims 1
BWWFVDDJLDDMIK-UHFFFAOYSA-N n-(4-morpholin-4-ylsulfonylphenyl)-2-piperidin-1-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)S(=O)(=O)N3CCOCC3)N=C(N3CCCCC3)N=C2CC1 BWWFVDDJLDDMIK-UHFFFAOYSA-N 0.000 claims 1
LNQFDPOWMMDZBT-UHFFFAOYSA-N n-(4-phenylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1C1=CC=CC=C1 LNQFDPOWMMDZBT-UHFFFAOYSA-N 0.000 claims 1
ZKXISLVKXDLAAL-UHFFFAOYSA-N n-(4-piperazin-1-ylsulfonylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC(C=C1)=CC=C1S(=O)(=O)N1CCNCC1 ZKXISLVKXDLAAL-UHFFFAOYSA-N 0.000 claims 1
URKVVTKWUDGZHO-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(methoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(COC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 URKVVTKWUDGZHO-UHFFFAOYSA-N 0.000 claims 1
NEWBGYVANRXSCX-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(piperidin-1-ylmethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(CN2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 NEWBGYVANRXSCX-UHFFFAOYSA-N 0.000 claims 1
KPFJDJSPOFTRKT-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-methylsulfanyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(SC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 KPFJDJSPOFTRKT-UHFFFAOYSA-N 0.000 claims 1
PDEXEQPXWVNVSV-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-phenyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 PDEXEQPXWVNVSV-UHFFFAOYSA-N 0.000 claims 1
KJNMKUGTDFIAPJ-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 KJNMKUGTDFIAPJ-UHFFFAOYSA-N 0.000 claims 1
VENAOHLCQXYNGR-UHFFFAOYSA-N n-(4-tert-butylphenyl)-7-(3-ethylsulfonylpyridin-2-yl)-2-propan-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound CCS(=O)(=O)C1=CC=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(C)(C)C)N=C(C(C)C)N=C2CC1 VENAOHLCQXYNGR-UHFFFAOYSA-N 0.000 claims 1
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AU2007227203A 2006-03-21 2007-03-21 6,7,8, 9 -tetrahydro- 5H- pyrimido [4, 5-d] azepin-4-yl] -amine derivatives as modulators of TRPVL for the treatment of pain Ceased AU2007227203B2 (en)

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US78541506P	2006-03-21	2006-03-21
US60/785,415		2006-03-21
PCT/US2007/007166 WO2007109355A2 (fr)	2006-03-21	2007-03-21	Tétrahydro-pyrimidoazépines utilisées comme modulateurs du trpv1

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US (3)	US8673895B2 (fr)
EP (1)	EP2024368B1 (fr)
JP (1)	JP5232768B2 (fr)
KR (1)	KR101461376B1 (fr)
CN (1)	CN101448835B (fr)
AR (1)	AR059985A1 (fr)
AU (1)	AU2007227203B2 (fr)
BR (1)	BRPI0709034B1 (fr)
CA (1)	CA2646977C (fr)
CR (1)	CR10387A (fr)
DK (1)	DK2024368T3 (fr)
EA (1)	EA017069B1 (fr)
EC (1)	ECSP088807A (fr)
ES (1)	ES2474152T3 (fr)
HR (1)	HRP20140664T1 (fr)
MX (1)	MX2008012163A (fr)
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NO (1)	NO341676B1 (fr)
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PE (1)	PE20080145A1 (fr)
PL (1)	PL2024368T3 (fr)
PT (1)	PT2024368E (fr)
RS (1)	RS53436B (fr)
SG (1)	SG177176A1 (fr)
SI (1)	SI2024368T1 (fr)
TW (1)	TWI440639B (fr)
UA (1)	UA92636C2 (fr)
UY (1)	UY30229A1 (fr)
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- 2007-03-21 AU AU2007227203A patent/AU2007227203B2/en not_active Ceased
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- 2007-03-21 UY UY30229A patent/UY30229A1/es not_active Application Discontinuation
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- 2007-03-21 US US11/726,756 patent/US8673895B2/en active Active
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- 2007-03-21 DK DK07753768.6T patent/DK2024368T3/da active
- 2007-03-21 CA CA2646977A patent/CA2646977C/fr active Active
- 2007-03-21 WO PCT/US2007/007166 patent/WO2007109355A2/fr not_active Ceased
- 2007-03-21 JP JP2009501567A patent/JP5232768B2/ja active Active
2008
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- 2008-10-08 EC EC2008008807A patent/ECSP088807A/es unknown
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- 2008-10-21 NO NO20084411A patent/NO341676B1/no not_active IP Right Cessation
- 2008-10-21 CR CR10387A patent/CR10387A/es not_active Application Discontinuation
2014
- 2014-01-17 US US14/157,671 patent/US9422293B2/en active Active
2016
- 2016-07-12 US US15/207,805 patent/US9738649B2/en active Active

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Publication number	Publication date
CR10387A (es)	2009-02-23
NI200800253A (es)	2012-11-30
JP2009530396A (ja)	2009-08-27
PL2024368T3 (pl)	2014-09-30
KR101461376B1 (ko)	2014-11-26
NO20084411L (no)	2008-11-03
RS53436B (sr)	2014-12-31
SI2024368T1 (sl)	2014-08-29
ZA200808975B (en)	2009-12-30
EA200802020A1 (ru)	2009-04-28
CN101448835B (zh)	2012-06-27
DK2024368T3 (da)	2014-05-19
US20160318942A1 (en)	2016-11-03
US8673895B2 (en)	2014-03-18
NO341676B1 (no)	2017-12-18
TW200813061A (en)	2008-03-16
TWI440639B (zh)	2014-06-11
NZ571343A (en)	2011-09-30
HRP20140664T1 (hr)	2014-10-10
BRPI0709034A2 (pt)	2011-06-21
US20140135311A1 (en)	2014-05-15
CN101448835A (zh)	2009-06-03
MX2008012163A (es)	2008-12-16
WO2007109355A2 (fr)	2007-09-27
EP2024368B1 (fr)	2014-04-30
AR059985A1 (es)	2008-05-14
JP5232768B2 (ja)	2013-07-10
US20070225275A1 (en)	2007-09-27
CA2646977A1 (fr)	2007-09-27
EP2024368A2 (fr)	2009-02-18
EA017069B1 (ru)	2012-09-28
HK1129888A1 (en)	2009-12-11
PE20080145A1 (es)	2008-02-11
ES2474152T3 (es)	2014-07-08
CA2646977C (fr)	2015-08-25
UA92636C2 (en)	2010-11-25
PT2024368E (pt)	2014-07-17
KR20090006098A (ko)	2009-01-14
WO2007109355A3 (fr)	2007-11-15
AU2007227203A1 (en)	2007-09-27
UY30229A1 (es)	2007-07-31
SG177176A1 (en)	2012-01-30
US9738649B2 (en)	2017-08-22
ECSP088807A (es)	2008-11-27
US9422293B2 (en)	2016-08-23
BRPI0709034B1 (pt)	2022-05-31

Publication	Publication Date	Title
AU2007227203B2 (en)	2013-01-10	6,7,8, 9 -tetrahydro- 5H- pyrimido [4, 5-d] azepin-4-yl] -amine derivatives as modulators of TRPVL for the treatment of pain
US20080004253A1 (en)	2008-01-03	Thiazolopyrimidine modulators of TRPV1
AU2007282535B2 (en)	2013-05-30	Pyrimidine derivative as PI3K inhibitor and use thereof
EP2224929B1 (fr)	2016-05-04	Modulateurs imidazolo-, oxazolo- et thiazolopyrimidines de trpv1
AU2014240388A1 (en)	2015-08-27	Substituted 7-azabicycles and their use as orexin receptor modulators
AU2011293584B2 (en)	2014-07-31	Sulfonylpiperazine derivatives that interact with glucokinase regulatory protein for the treatment of diabetes
US20090156598A1 (en)	2009-06-18	Imidazolopyrimidine modulators of TRPV1
HK1129888B (en)	2015-02-06	6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepin-4-yl]-amine derivatives as modulators of trpv1 for the treatment of pain
HK1147952B (en)	2017-06-30	Imidazolo-, oxazolo-, and thiazolopyrimidine modulators of trpv1

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